Artificial musk



Patented Sept. 12, 1933 UNITED STATES PATENT OFFICE ARTIFICIAL MUSK John William Borman, Glen Ridge, N. J., as-

signor to Harold H. Fries, doing business as Fries Bros, New York, N. Y.

No Drawing. Application April 4, 1932 Serial No. 603,211

3 Claims.

rivative of 1,3-dimethy1-4-aceto-6-tertiarybuty1- benzene. Musk Ambrette is the dinitro derivative of 1-methyl3-methoxy-G-tertiary-butylbenzene. Of these artificial musks, the Musk Ketone is considered as having the finest odor, and the Musk Ambrette as having the strongest odor.

According to my present invention, I have found that by introducing another tertiary butyl group in the intermediate used in the production of Musk Ambrette, that is, in the 1-methyl-3- methoxy-6-tertiary-butyl-benzene, so as to form 1-methyl-3-methoXy-4 6-ditertiarybutylbenzene, I obtain a product which upon nitration yields a dinitro derivative having a pronounced odor of musk, and which in fineness of odor and strength is intermediate between Musk Ketone and Musk Ambrette.

My artificial musk may be produced as follows: To a mixture of 820 grams of 1-methyl-3-methoxy-B-tertiary-butyl-benzene and 695 grams of tertiary butyl alcohol, there is allowed to flow, under vigorous stirring and cooling so as to keep the temperature at about C., 550 grams of concentrated sulphuric acid. 500 cc. of a solvent such as Xylol is then added and the product Washed with water until free from acid, and when it is found to be neutral it is dried and fractionally distilled. The uncombined l-methyl-B- methoxy-S-tertiary-butyl-benzene is recovered, and can be again used. The fraction coming over between 120 and 130 C. at 45 mm. contains the 1-methyl-3-methoxy-4, G-ditertiarybutyl-benzene required for further treatment. F To this fraction is added an equal volume of methanol, from which the desired product crystallizes out, and, upon filtering, washing and drying, it is obtained in the form of white crystals having a congealing point of 57.5 C. This product, which may be considered as an intermediate for use in the preparation of artificial musk is,

to the best of my knowledge, a new chemical product.

140 grams of this crystallized product is slowly added to 1400 grams of 95% nitric acid, under constant stirring at a temperature held between -5 and +5 C. When all the crystalline product has been added, the mixture is allowed to stand for some time, after which it is poured onto ice water and the reaction product, which is in the form of an oil, is extracted with toluol, washed 1 until neutral, and the toluol recovered in vacuum. The weight of the crude nitrated product will be approximately 155 grams. On crystallizing this from methanol twice, it is obtained in its pure state in the form of white, shiny crystals which are insoluble in water, somewhat S0111? ble in 95% ethyl alcohol, and readily soluble in methanol and acetone and having a melting point of 11l.8-113.2 C. This substance is a new chemical compound having the characteristic musk odor.

While I have described but a single method of preparing the new chemical compound having the odor of musk, it is to be understood that my invention is primarily directed to said product, and not any method of preparing the same, since such may be varied Without departing from the spirit of my invention.

What I claim is:

1. The chemical compound 1-methyl-3meth oxy-i, 6-ditertiary-butyl-2, 5-dinitro-benzene, said compound having a melting point of 111.8 to 113.2" C.

2. The method of making artificial musk which comprises nitrating l-methyl-3-methoxy-4, 6-ditertiary-butyl-benzene to obtain the dinitro derivative thereof.

3. The method of making artificial musk which comprises introducing a tertiary butyl group into 1-methy1-3-methoxy-6-tertiary-butyl-benzene, 5 and nitrating the resulting l-methyl-S-methoxy- 4, 6-ditertiary-butyl-benzene to obtain the dinitro derivative thereof.

JOHN W. BORMAN. 

